Keep in mind, your policy is covering 2 parts - the property (includes damage to the structure, any contents you own, and loss of rent) and the general liability (Ex. a lawsuit from a slip & fall on a sidewalk that resulted in an injury).

They aren't unrealistic issues/concerns but I feel he wont pull the trigger unless he's 100% sure there isn't a risk and in his principle and in real estate there isn't such a guarantee.

I'm also thinking that in many places a change in ownership is also a trigger at the appraisal district to review the value.   

I'm too scared to pull the trigger on my flip right now despite all that I just mentioned. 

I was fortunate enough to have this at the time, but if I had any advice, I would focus on building a great team before you pull the trigger.

No kidding, sounds great, let’s pull the trigger on it.

Not sure what the bank reporting triggers there are, but what other ways can he close transaction? 

  (1 of my clients had this claim in Nov 2019).2)  Bodily Injury claims (contractor or contractors employee) gets hurt and doesn't have work comp. 

See the article below for some infohttps://rsmus.com/what-we-do/services/tax/the-dilemma-of-dealer-or-investor-classification-for-real-estate.html-If you feel meet the investor designation the next trigger is how long you hold the property, if it’s less than a year you will be subject to short term capital gains, if more than one year it will be long term Capital gains.

I pulled the trigger.